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A compound based on diaryl ketone and its application in OLED devices

A technology of diaryl ketones and compounds, applied in the fields of electrical solid state devices, semiconductor devices, chemical instruments and methods, etc., which can solve the problems of difficult exciton utilization, high fluorescence radiation efficiency, low S1 state radiation transition rate, and efficiency roll-off And other issues

Active Publication Date: 2019-04-09
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although theoretically TADF materials can achieve 100% exciton utilization, there are actually the following problems: (1) The T1 and S1 states of the designed molecules have strong CT characteristics, and the very small S1-T1 state energy gap, although it can High T through TADF process 1 →S 1 state exciton conversion rate, but at the same time lead to a low S1 state radiative transition rate, therefore, it is difficult to have both (or simultaneously achieve) high exciton utilization efficiency and high fluorescence radiation efficiency; (2) Even if doped devices have been used to alleviate the T excitation Subconcentration quenching effect, the efficiency of most TADF material devices has a serious roll-off at high current densities

Method used

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  • A compound based on diaryl ketone and its application in OLED devices
  • A compound based on diaryl ketone and its application in OLED devices
  • A compound based on diaryl ketone and its application in OLED devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: the synthesis of compound 2

[0073] synthetic route:

[0074]

[0075] In a 250ml four-neck flask, under a nitrogen atmosphere, add 0.01mol 4,4'-dibromobenzophenone, 0.025mol intermediate A1, 0.04mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 98.8% and a yield of 63.2%.

[0076] Elemental analysis structure (molecular formula C 69 h 42 N 4 o 3 ): theoretical value C, 84.99; H, 4.34; N, 5.75; 0, 4.92; test value: C, 84.96;

[0077] HPLC-MS: The molecular weight of the material is 975.10, and the measured molecular weight is 975.33.

Embodiment 2

[0078] Embodiment 2: the synthesis of compound 9

[0079] synthetic route:

[0080]

[0081] In a 250ml four-necked flask, under nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.012mol intermediate A2, 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampled and plated, the reaction was complete; naturally cooled, filtered, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product with a purity of 99.2% and a yield of 73.5%.

[0082] Elemental analysis structure (molecular formula C 44 h 32 N 2 o 2 ): theoretical value C, 85.14; H, 5.20; N, 4.51; 0, 5.15; test value: C, 85.15;

[0083] HPLC-MS: The molecular weight of the material is 620.74, and the measured molecular weight is 620.87.

Embodiment 3

[0084] Embodiment 3: the synthesis of compound 16

[0085] synthetic route:

[0086]

[0087] In a 250ml four-neck flask, under nitrogen atmosphere, add 0.01mol 4-bromobenzophenone, 0.012mol intermediate B1, 0.03mol sodium tert-butoxide, 5×10 -5 mol Pd 2 (dba) 3 , 5×10 -5 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling point plate, the reaction was complete; natural cooling, filtration, filtrate rotary evaporation, silica gel column, the target product was obtained with a purity of 99.2% and a yield of 75.3%.

[0088] Elemental analysis structure (molecular formula C 53 h 36 N 2 o 2 ): theoretical value C, 86.86; H, 4.95; N, 3.82; 0, 4.37; test value: C, 86.85;

[0089] HPLC-MS: The molecular weight of the material is 732.87, and the measured molecular weight is 733.06.

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Abstract

The invention discloses a compound based on diaryl ketone and its application on organic electroluminescent devices. Groups can improve the thermal stability of the material. The compound of the present invention is applied to an organic electroluminescent device as a light-emitting layer material, and the light-emitting device using the compound of the present invention has good photoelectric performance, and can better adapt to and meet the application requirements of panel manufacturers.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a compound containing diaryl ketone and its application as a light-emitting layer material in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] However, traditional organic fluorescent materials can only use 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). The external quantum efficiency is generally lower than 5%, and there is still a big gap with the efficiency of phosphorescent devices. Although phosphorescent materials enhance intersystem crossing due to the strong spin-orbit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12C07D413/04C07D265/34C07D221/18C07D241/38C07D491/048C07D498/06C07D471/06C07D498/04C07D401/14C07D265/38C07D219/08C07D219/02C07D513/04C09K11/06H01L51/54
CPCC09K11/06C07D219/02C07D219/08C07D221/18C07D241/38C07D265/34C07D265/38C07D401/14C07D413/04C07D413/12C07D471/06C07D491/048C07D498/04C07D498/06C07D513/04C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1044H10K85/657H10K85/6572H10K50/11
Inventor 王立春张兆超李崇徐凯叶中华
Owner JIANGSU SUNERA TECH CO LTD
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